Just wanted to get some opinions on what would be easier as far as access to HA from outside the network. I have a Pi2 running all-in-one with a TP-Link ONHUB as my router. Wondering which would give me a better experience and security: using the Tor route, or going with Duck DNS and letsencrypt?
Thanks 
It depends whether you want to access you machine from all machines. Maximum security would be TOR but you wont be able to access HA on a phone from external as easily as with SSL. Furthermore for things like alexa TOR would not work.
Cheers
Awesome! Didn’t know about alexa not working with TOR. I don’t have one now but I plan on adding one in the future (or maybe the Google Home) so I think ill try SSL. Thanks for the help!